Question: I'm not sure my friend is ready for this- How do I help him?

Dear Lounge Advice,

My best friend since my college days recently went through a horrible divorce. His relationship was completely vanilla and he's only had sex with one girl in his entire life (his ex-wife).

He's known me since school and knows I've been involved in the lifestyle even before I knew what the phrase meant. This guy is pretty much the kind of guy most women dream about: Wealthy, self made, herculean GQ-model complete with a heart of gold and he wants to experiment in the "lifestyle"... but I'm really not sure he's ready for it.

Well, I would just sit down and have a casual chat with him about it. Give him some inside info about what is expected of single males. The most important thing to emphasize to him is that this lifestyle is about couples, and he will be an accessory. As such, he will need to realize that attachment to the woman is a big no-no. Of course he will agree, but this can sometimes happen when singles get involved with couples.
How am I sure of this? I've seen it happen, and it has happened to me with a small handful of single males that I have played with. Admittedly, my current husband was a single male playmate who fell in love with me. But that's a story for another day.
He also needs to know no matter how hot he is, he needs to build a reputation, and this takes a while. Advise him to take this very slowly and set up a profile just to take a look around and get a good feeling about this lifestyle. If you can, direct him to some of the single male advice in the archives here that I have given in the past. I am pretty well-versed in the single male formula for success, and it is detailed in the archives.
He will also need to practive a lot of patience. This lifestyle is harder for single males, and he shouldn't feel offended if things don't click immediately for him, regardless of his attributes.

You may not think he's ready for it, but let's play devil's advocate. He has been with one one woman- perhaps it's time for him to experience this side of life. I'm not saying that his long-time monogamy was a bad thing, but he may want to balance that out with some wild experiences just to know what it feels like to live with a bit of wild abandon.
Tell him not to go into this expecting to find a single female playmate to join him. Although this is a great hope, it's not realistic. If he truly adheres to the code of gentlemanly conduct in this lifestyle, this may find him in time (if he ever does desire it).

Really, this is up to him. It is up to him whether he is ready for it or not. You probably won't change his mind anyways. The best thing is to drive his desires in the right direction.
If he joins LL, use me a resource. I'm always willing to chat/IM/answer any questions for beginners to help them feel successful.